Dimethylformamide → HCID 86660175, compound

HRID 454931Notes

Reaction equation

HRID 454931 reaction equation
[H-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1.Cl[C:21]1[C:22]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=N[CH:24]=[CH:25][N:26]=1.[CH3:40]N(C=O)C>CCOC(C)=O.O>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[N:13]1[CH2:14][CH2:15][CH:16]([O:19][C:21]2[C:22]([CH:27]3[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:31][CH2:32]3)=[CH:40][CH:24]=[CH:25][N:26]=2)[CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 40516418HCID 40516418, compoundHCID 58547013Tert-butyl 4-(3-chloropyrazin-2-yl)piperidine-1-carboxylate

Product 1

HCID 86660175HCID 86660175, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 254 mg, 10.58 mmol) was added to a solution of 1-(quinolin-2-yl)piperidin-4-ol (see PREPARATION P1.1; 805 mg, 3.53 mmol) in DMF (16.8 ml) under an atmosphere of nitrogen and the mixture was stirred for 15 mins at RT. Tert-butyl 4-(3-chloropyrazin-2-yl)piperidine-1-carboxylate (see PREPARATION P16.1; 1050 mg, 3.53 mmol) was next added, and the mixture was heated at 100° C. After the reaction was complete, the mixture was cooled to RT and diluted with EtOAc and water. The layers were separated and the aqueous was extracted with EtOAc (2×). The combined organic layers were dried over sodium sulfate, filtered and concentrated and used in the next step without further purification.

Workup

  1. temperaturethe mixture was heated at 100° C
  2. temperaturethe mixture was cooled to RT
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with EtOAc (2×)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customused in the next step without further purification

Sources & evidence

ORD record
ord-24c8d260fab84e3dba9044f45ce64f78
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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